But for the left-hander to be on his way to Queens and not the Bronx? Few would have anticipated that, and that almost certainly included Yankees senior vice president Hank Steinbrenner.
In the end, the Yankees decided the cost of acquiring Santana would have been too prohibitive, both in terms of the financial sums involved and also the package of young players the Twins anticipated in return.
Though Steinbrenner's desire for the two-time Cy Young Award winner was unquestionable -- as well as his candor and bluster in discussing the Hot Stove heartthrob -- other factions of the Yankees organization favored staying the course.
Hal Steinbrenner, a general partner of the club heavily invested in financial matters, was known to be opposed, as was Yankees general manager Brian Cashman, who favored keeping the pitching staff intact through its transition.
The latter had confirmed the club's stance in recent days, doing so publicly last week while speaking at William Paterson University in Wayne, N.J.
"My strong recommendation is that we stick with our young pitching and keep it in-house," Cashman said, drawing cheers from an audience of about 900.
Cashman and Steinbrenner were unavailable for comment on Monday.
With Santana apparently on his way over the Triboro Bridge to Shea Stadium -- needing only a contract extension to confirm a workload ripe with weak-hitting pitchers and defense-friendly dimensions -- the Yankees remain on track as pitchers and catchers begin to filter into Legends Field in Tampa, Fla.
Showcasing their "Big Three" pitching prospects of Joba Chamberlain, Phil Hughes and Ian Kennedy as strong contenders for the rotation, the Yankees plan to have six men vying for five slots, joined by Chien-Ming Wang, Andy Pettitte and Mike Mussina.
They were considered favorites at one point to add Santana, though, and the Yankees did little to hide their interest. Pushing forward in early December, Steinbrenner's outspoken fashion left no doubt and prompted many to speculate a major announcement could be made in Nashville.
Though initially reluctant to offer the 21-year-old right-hander Hughes in a trade proposal, the Yankees eventually relented, putting Hughes on the table as part of a four-player package that also reportedly included outfielder Melky Cabrera, right-hander Jeff Marquez and infielder Mitch Hilligoss.
Keeping the Red Sox involved, Twins general manager Bill Smith reportedly used the opportunity to press for more. The Yankees, insiders insisted, would not include both Hughes and 23-year-old right-hander Kennedy in the same trade.
Some speculated that Boston and New York had been pitted against each other to create a bidding war; that maneuver prolonged the process and effectively snuffed out chances of reaching a final decision in Nashville.
While Cashman played it coy, refusing to as much as acknowledge that the Twins possessed a left-handed pitcher named Santana, Steinbrenner wasn't nearly as shy. Through Steinbrenner, the Yankees issued an ultimatum that if a deal was not reached by the final day of the Winter Meetings, the Hughes package would be pulled.
Though Cashman and Smith maintained intermittent contact for weeks after, the Yankees seemed prepared to fade into the backdrop of the Santana rumor mill, allowing the Red Sox and Mets to jockey for status as the media's front-running choice.
With a finish line in sight, the daily routine of monitoring Steinbrenner for the latest blow-by-blow accounts of activity with the Twins should cease. Admitting recently that even he had been beginning to waver on his stance for putting Santana in pinstripes, Steinbrenner has said that he is comfortable with keeping the rotation as is.
Then again, if the Yankees' non-pursuit of Santana turns out to be a misstep in Steinbrenner's eyes, some in the hierarchy could be held accountable.
Steinbrenner said as much in a lengthy interview last week with The Associated Press in his Legends Field office. The young elephants may be in the tent, but let there be little doubt: The Boss, and all that title stands for in the Yankees universe, is alive and well.
"I will be patient with the young pitchers and players. There's no question about that because I know how these players develop," Steinbrenner said. "But as far as missing the playoffs -- if we miss the playoffs by the end of this year, I don't know how patient I'll be.
"But it won't be against the players. It won't be a matter of that. It will be a matter of maybe certain people in the organization could have done something else."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.